Water → 3-Methylthio-4-chromanone

HRID 988943Notes

Reaction equation

HRID 988943 reaction equation
[SH3+:1].[Br:2][CH:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4]1.O.[Na].[CH3:16]S>C(O)C>[Br:2][CH:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4]1.[CH3:16][S:1][CH:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4]1

Participants

7

Reactant 4

HCID 962Water2×HCID 3015009SulfoniumHCID 123873063-Bromochroman-4-one2×HCID 45051789Methylmercaptan sodium

Product 2

HCID 120675283-Methylthio-4-chromanoneHCID 123873063-Bromochroman-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The sulfonium salt compound expressed by structural formula [6] was synthesized as follows. First, the present inventor prepared 3-bromo-4-chromanone. The 3-bromo-4-chromanone was synthesized in accordance with the report by W. S. Johnson et. al. in J. Am. Chem. Soc., vol. 66, pages 218-220, 1944. 10.4 grams of 3-bromo-4-chromanone was dissolved in 42 milli-litters of ethanol. 21.3 milli-litters of 15% water solution of methyl-mercaptan sodium salt was dropped thereinto. The resultant solution was agitated at room temperature for 2 hours, and the resultant mixture was poured into cold water. An organic layer was extracted by using 200 milli-litters of ether, and the ether layer was washed in sodium chloride and, thereafter, water. The ether layer was dried by using magnesium sulfate, and the solvent was removed in low pressure. The residue was put in a silica gel column. Using eluate containing hexane and ethyl acetate at 3:1, the residue was separated and refined. Then, 1.52 grams of 3-methylthio-4-chromanone was obtained. The yield was 17%.

Workup

  1. customwas synthesized
  2. extractionAn organic layer was extracted
  3. washthe ether layer was washed in sodium chloride
  4. dry with materialThe ether layer was dried
  5. customthe solvent was removed in low pressure
  6. additionUsing eluate containing hexane and ethyl acetate at 3:1
  7. customthe residue was separated

Sources & evidence

ORD record
ord-4d40b44aa06649d5b7f0ea9739e657ee
Source dataset
uspto-grants-2003_10
Patent number
US06638685B2

Reaction notes

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